Virginia has been serving up memorable meals for centuries, and some of its oldest restaurants still welcome hungry travelers today.
This road trip connects seven longtime favorites where the stories are almost as interesting as the food, with stops dating from the 1700s through the early 1900s.
You’ll even find connections to Founding Fathers, railroad dining cars, classic drive-in service, and buildings that witnessed major chapters of American history.
With so much history packed between each meal, come hungry because this tasty drive through Virginia has seven delicious stops waiting ahead.
1. Doumar’s Cones & Barbeque — Norfolk
Doumar’s Cones & Barbeque started with Abe Doumar, whose experience at the 1904 St. Louis World’s Fair inspired him to build a four-iron waffle machine.
After opening his first ice cream stand in 1905, Abe opened another in Norfolk in 1907, before the business moved to its current location at 1919 Monticello Ave.
When you visit, start with a fresh waffle cone packed with creamy ice cream, then try the famous barbecue sandwich with slow-cooked pork and tangy slaw.
You can eat inside or enjoy classic carhop service outside, where food arrives at your vehicle just like it did during America’s drive-in heyday.
2. Virginia Diner — Wakefield
Next, drive about an hour to Wakefield, where Virginia Diner has been feeding hungry travelers at 408 North County Drive since opening in 1929.
What started as a restaurant inside a railroad dining car is now a spacious dining room serving country ham steak, fried chicken, Brunswick stew, and warm biscuits.
For dessert, try the peanut pie, a sweet house favorite loaded with crunchy toppings, then check out the diner’s old photos and memorabilia displayed along the walls.
Before you leave, keep the peanut theme going with a stop at the country store, where you’ll find locally grown Virginia peanuts in salted and candied varieties.
3. New York Deli — Richmond
From Wakefield, continue about an hour to Richmond’s Carytown, where New York Deli has been a local staple at 2920 West Cary Street since 1929.
This is where the iconic Sailor Sandwich was born, combining hot pastrami, grilled knockwurst, Swiss cheese, and spicy mustard on toasted rye bread.
If you want to explore more of the menu, try the Reubens, chicken & waffles, crab cakes, nachos, and other deli classics before heading up to the rooftop bar.
With Carytown’s colorful boutiques and the historic Byrd Theatre just steps away, this is an easy food stop to work into a day of shopping and sightseeing.
4. Hanover Tavern — Hanover
After New York Deli, drive around 25 minutes to Hanover Tavern at 13181 Hanover Courthouse Road, a historic stop with roots dating back to the 1750s.
Patrick Henry once lived here after marrying Sarah, daughter of tavern owner John Shelton, adding a fascinating connection to one of Virginia’s Founding Fathers.
Today, you can order Southern favorites like shrimp and grits, fried catfish, and crab cakes inside rooms that blend historic architecture with a full-service restaurant.
Once you’re full, check out the tavern’s exhibits or catch a show at the on-site Bradley Theater, making this more than just another food stop.
5. The Virginian — Charlottesville
Just 1 hour and 15 minutes from Hanover Tavern is The Virginian, which has called 1521 University Avenue on “The Corner” near the University of Virginia home since 1923.
Known as Charlottesville’s oldest restaurant, it has spent more than a century serving students, professors, locals, and road-trippers from its narrow storefront.
Come hungry for the popular Stumble Down Mac N’ Cheese, made from scratch with creamy pepper jack macaroni and cheese topped with a cheddar potato cake.
You can also dig into favorites like Virginian Club, a crab cake sandwich, Southern fried chicken, BBQ nachos, or baby back ribs if you’re craving something heartier.
6. Texas Tavern — Roanoke
A 2-hour drive from The Virginian takes you to Texas Tavern, a Roanoke institution with just 10 counter seats at 114 West Church Avenue, dating back to 1930.
The family-run restaurant stays open 24 hours a day, making it a classic spot for breakfast, lunch, dinner, or a seriously late-night snack.
Whenever you stop by, order the Cheesy Western, a cheeseburger topped with a fried egg, or try a bowl of its chile made from a secret recipe with roots in Texas.
From your seat, watch your meal come together behind the counter while soaking up one of the city’s longest-running dining traditions.
7. The Tavern — Abingdon
Finish your Virginia restaurant road trip with a 2-hour drive to Abingdon, where The Tavern occupies a historic building dating back to 1779 at 222 East Main Street.
Originally built as a tavern and inn, the structure has also served as a post office, hospital for wounded Civil War soldiers, and gathering place during its long life.
Today, settle in for a meal inside the restored building, where the menu features wienerschnitzel, stuffed filet mignon, German-inspired favorites, beer, and cocktails.
Look for old-school architectural details as you eat, then walk about ten minutes along Main Street to the landmark Barter Theatre, which opened in 1933.
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